Nitric Acid → HCID 14838332, compound

HRID 1756827Notes

Reaction equation

HRID 1756827 reaction equation
[N+:1]([O-])(O)=O.[Cl:5][C:6]1[C:11]2[CH2:12][C:13]([CH3:16])([CH3:15])[O:14][C:10]=2[C:9]([C:17]([OH:19])=[O:18])=[CH:8][CH:7]=1>S(=O)(=O)(O)O>[NH2:1][C:7]1[CH:8]=[C:9]([C:17]([OH:19])=[O:18])[C:10]2[O:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]=2[C:6]=1[Cl:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 14838229HCID 14838229, compound

Product 1

HCID 14838332HCID 14838332, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

To a mixture of 40 ml of nitric acid and 40 ml of sulfuric acid cooled to 5° C. by means of an external ice bath were added 10 g of 4-chloro-2,2-di-methyl-2,3-dihydro-7-benzofurancarboxylic acid over a period of 28 minutes. After stirring at 5° C. for 10 minutes, the mixture was added to ice with stirring. The resulting solid was collected by filtration and washed with water. After air drying, the residue was crystallized twice from ethyl acetate/hexane to provide 3.5 g of the desired subtitle intermediate, m.p. 260°-262° C.

Workup

  1. additionthe mixture was added to ice
  2. stirringwith stirring
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customAfter air drying
  6. customthe residue was crystallized twice from ethyl acetate/hexane

Sources & evidence

ORD record
ord-9d4b8d8434a54794aa9fd2bcd3ff087c
Source dataset
uspto-grants-1995_08
Patent number
US05442078

Reaction notes

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